When Swamp Dogg first began work on his latest album, he had only one guiding principle.

“I just didn’t want it to sound like Swamp Dogg,” says Jerry Williams, who for close to a half-century has recorded his singular blend of eccentric soul under that name. “This time,” says the singer, 76, “I wanted to shock the shit out of them.”

Ever since he began making records as Swamp Dogg in the early Seventies, Williams has never much worried about how his music would fit into the larger American pop landscape. But the singer-songwriter-producer’s two most recent records — 2009’s holiday downer An Awful Christmas and a Lousy New Year and 2014’s left-field The White Man Made Me Do It — had failed to register, even by Swamp Dogg’s own expectation-defying standards.

The concept for Love, Loss and Auto-Tune, Williams’ miraculously inventive new collection, “came from me wanting to start reinventing myself and get out of the rut that I was in,” he says. “My last few records were basically the same thing; you could hear the same production. I said, ‘Hell, I really don’t have much to lose if I go out on a ledge,’ so I went out on a ledge.”

The album, which finds Williams teaming up with Poliça’s Ryan Olson and Bon Iver’s Justin Vernon, producers and musicians several generations his junior, represents an artistic rebirth of sorts for the soul veteran. The album filters its source material — which ranges from Fifties R&B– and Seventies-soul–inspired originalsto Great American Songbook standards — through dissonant, aggressively Auto-Tuned production from Olson and longtime Swamp Dogg producer Larry “MoogStar” Clemon, with Vernon providing additional help on vocal processing.

Williams originally met Olson a few years ago through a mutual contact. The two discussed a re-release of an old project Williams had been involved in, and while the reissue fell through, they remained friends. Williams had already recorded a more crude, rough version of Love, Loss and Auto-Tune with MoogStar, but when Williams told Olson about the project, Olson asked if he could be involved. Olson recruited Vernon, and the duo spent several years refining, fine-tuning, and deconstructing Williams and MoogStar’s recordings until they arrived at a finished product.

“I was kind of depressed, so I had the best time working on this music,” says Justin Vernon. “I ended up putting a bunch of time into it, but nowhere near as much time as Ryan. To be a cadet and a lieutenant on the sidelines felt really awesome.”

“We just took things a little further,” says Olson. “You don’t usually hear a person with Swamp’s voice singing through those sounds and taking it to the kinds of dissonant places that he takes it. When he heard it, he wasn’t weirded out. He was all for it. He’s way more progressive than most.”

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“I’m real opinionated about my shit,” says Williams. “I wasn’t this time. When Ryan sent the stuff back, I just loved it to death. I had never heard myself like that. I fell in love.”

On his new collection, Williams meditates in equal parts on loneliness and lust. Personal and practical concerns receive equal weight, from the tragicomic wealth-gap blues of “$$$ Huntin’” to the existential dread of “I’ll Pretend.” Vernon’s favorite song is “Sex With Your Ex,” a devotional ode that treats the generally frowned-upon practice as a righteous spiritual salve. The album is littered with Swamp Dogg’s oddball lyrical wit; from one song to the next, he’ll coo about the divine properties of black negligees and “Chanel #69” before launching into an extended diatribe about how crowded Walmart has become since the recession.

The flurry of financial, emotional and interpersonal drama on the album are, in part, a reflection of the singer’s chaotic everyday life. When Rolling Stone called the singer at his longtime Los Angeles home recently, he sounded flustered at first. “My day has been a little hectic,” he told me. “I had a painter at the house, and I owed him $220 more dollars, but I only had $209 dollars. He’s hassling me about the 10 dollars or some shit, and I only had a 20. He didn’t have a 10. I guess he left here a little pissed.”

“All of my problems can be solved with money,” he explain a little later, “and that’s the way I usually solve them.”

“There are those rebels out there who make a lot of noise and their brand, almost, is being a rebel,” says Justin Vernon. “But Swamp just doesn’t give a fuck. You look at everything he’s done since the Fifties and you’re able to say, ‘Wow, this dude is on his own trip.’ He just understands that in life, you get one shot, you do what you feel like doing, try to get paid. But if not, you just enjoy it.”

Growing up in Portsmouth, Virginia, Williams, who was born in 1942, remembers his family listening to everything on the radio, from standards to jump blues and country. “My house was a party,” he says today, “and they partied.”

In grade school talent shows, he sang country songs like ”Peace in the Valley” by Red Foley, “Hadacol Boogie” by Bill Nettles. But Williams settled on his artistic destiny, when, as a kid, he first saw Fats Domino perform a local show in the area. “All those guys that I fell in love with played piano and sang, and that’s what I wanted to do,” he says.

Williams made his recording debut at age 12, releasing a rollicking early rock & roll number called “HTD Blues” in 1954 under the name “Little Jerry Williams.” Over the next decade-plus, Williams became a prolific songwriter and recording artist, an expert in pastiche who was equally at home performing bubble-gum soul, pop-inflected blues, Jerry Lee Lewis–style rockabilly and Fats Domino–inspired boogie.

But it wasn’t until Little Jerry Williams, fed up with the exploitative Sixties music industry and the pressures of commercial songwriting, reinvented himself as Swamp Dogg in 1970 that the artist finally settled on his enduring voice.

“I became Swamp Dogg in 1970 in order to have an alter-ego and someone to occupy the body while the search party was out looking for Jerry Williams, who was mentally missing in action due to certain pressures, mal-treatments and failure to get paid royalties on over 50 single records,” Williams once wrote. “I wanted to sing about everything and anything. … Commencing in 1970, I sung about sex, niggers, love, rednecks, war, peace, dead flies, home wreckers, Sly Stone, my daughters, politics, revolution and blood transfusions. … Recording in Alabama and sincerely singing/writing about items that interested me gave birth to the name Swamp Dogg.”

Swamp Dogg’s first two albums, 1970’s Total Destruction to Your Mind, and 1971’s Rat On! were urgent commentaries on late-stage Vietnam war desolation and post-Sixties burnout that introduced Williams as a resurgent voice in a genre, Southern soul, that had already lost much of its commercial and cultural relevance by the end of the decade.

“Houses are paper but folks don’t hear a word you say,” Swamp sings on 1970’s poetic “Synthetic World. “Friendship’s like acid/It burns as it slides away.”

But like “Synthetic World,” songs like “Hey Redneck” and “God Bless America For What,” were aggressive, confrontational statements that proved uncomfortable for mainstream audiences, and within a few years, it was clear that Swamp Dogg would not be heard by the masses. Today, however, the albums, since reissued, are cult classics that have influenced generations of younger musicians.

“The first song I ever heard of Swamp Dogg was ‘Total Destruction to Your Mind,’” says one such artist, Lee Bains, frontman for the Southern roots-punk band Lee Bains and the Glory Fires. “It sounds like almost like Wilson Pickett’s ‘Hey Jude,’ but then the lyrics come, and you realize: This is not Wilson Pickett. It was psychedelic but also aggressive, the idea of destruction. White audiences were so fearful of black power, and then you have this obviously really smart, intellectual black singer singing lyrics, which are more erudite than your typical pop song, speaking with such bombastic and potentially violent language, but doing so in this very fun, supercharged, very Southern black sound.”

“A lot of times Southern music of that era plays to the common idea of the Southerner as a simpleton,” Bains continues. “When I first heard Swamp Dogg, I was really taken by the fact that nobody can listen to Swamp Dogg and consider him a simpleton. His vocabulary is huge. He’s talking about really complicated things in nuanced ways, and it’s very clever.”

As the title of his new album suggests, the sources of Swamp Dogg’s dive into Auto-Tune are rather personal. The singer can be heard practically grieving in real time on songs like “Lonely,” “I’ll Pretend” and the cover of the 1953 standard “Answer Me, My Love,” pained confessionals that find the singer mourning the loss of his first wife and former manager, Yvonne Williams, who died in 2003.

“I didn’t really know what loneliness was until she passed,” says Williams 15 years later. “Before, when I would write songs about loneliness in other people, I was just writing about people I knew, things they had said about their breakups, that kinds of stuff. This time, I am, seriously, lonely. I got a girlfriend, but that doesn’t fill up the space. Matter of fact, her husband died and she got a space that she can’t fill up too, so we’re both trying to put 10 pounds of shit in a five pound bag. It’s good, it’s still great, but when I was writing this record, I had to put myself in the mood of ‘Hey, you ain’t gonna see Yvonne no more. So you need to get up and get to work,’ because that’s what she would tell you to do.”

The singer turned to Auto-Tune as a sort of emotional mask, a way of allowing himself to communicate a stark vulnerability that he otherwise wouldn’t have felt comfortable expressing so plainly. “I didn’t want you to be able to hear my voice and determine what state of mind I was in,” he says.

“Lonely,” a devotional to his late wife, begins with Swamp Dogg repeating the refrain “I’m so lonely” over a Sixties-soul-revue piano riff. “That comes from the gut,” the singer says. “I feel kind of sad every time I sing it.”

Williams merges his emotional and economic struggles on the song “I Love Me More,” a harsh, New Jack Swing–inspired self-care manifesto that came about when he realized, after years of giving away significant portions of money to friends and associates in need, that he needed to start taking better care of himself.

“What happened was a girl kept asking me for financial assistance and wanted me to help out,” he says. “I thought, this is a good person, so I counted my money, but it wasn’t right. In order to be able to do what I needed to do, that’s where I finally had come out and say, ‘Look, I’ve also got a bill to pay. You know, I love you, but I’m in a mode that I never used to be in, and that’s: I love me more.’”

It’s yet another lesson that Williams learned from his late wife, Yvonne. “I’m a sucker for a sob story,” he says. “Yvonne always used to say, ‘You give everything away. You give everything to other people. You gotta stop it, because it’s gonna backfire on your ass.’”

All of that was on his mind when he wrote “I Love Me More” just a few years ago: the faith and support of his longtime love and the idea that after nearly 65 years as a recording artist, Swamp Dogg no longer needed to take care of anyone but himself — a concept he sums up with the declaration “I love you, but I love me more.”

“I might still be trying to convince myself,” he says, before saying goodbye.